Refine Search
Map
Sort by
$875,000
970333 MLS
Beautiful 5.84 acre parcel located on the heart of the North Fork. Zoned residential (AC), this property offers endless potential for a private home or vacation retreat. The expansive lot features serene natural surroundings, ample space for development and is ideal for creating your dream property. Whether you're looking for a peaceful lifestyle or an investment opportunity, this property combines North Fork charm with versatile residential zoning.

15690 County Road 48, Cutchogue
$1,750,000
4 Beds ⋅ 2 Baths ⋅ 967817 MLS
Set on 1.16 acres of beautifully landscaped and private grounds, this charming North Fork property offers space, versatility, and serene farm vistas. The main home features 4 bedrooms, 1.5 baths, an eat in kitchen, living room, and sitting area filled with natural light. A remarkable 6 car garage currently houses a Michael Phelps lap pool with hot tub and sauna, creating a unique year round wellness retreat and offering endless possibilities for a contractor, artist, car enthusiast, or home gym. A separate guest house barn with wood burning stove provides additional comfort and flexibility. Solar panels with EV charging keep electric costs extremely low, approximately $17 per month. Central air, oil heat, and public water add convenience. Cutchogues’ Causeway Beach ,Mature landscaping, exceptional privacy, and room for a pool or tennis or pickleball court complete this special offering.

3275 Skunk Lane, Cutchogue
$3,750,000
3 Beds ⋅ 5 Baths ⋅ 963336 MLS
SOUND FRONT RETREAT - Designed in 1986 by architect Sanford Hanauer for his own residence and reimagined in 2011, this elegant homestead is modern luxury done the right way. Set high above the shoreline on 2.45 acres with 200 feet of direct beachfront, angled so the water is the constant-nearly every room, every day, every season. Floor-to-ceiling glass pulls in the light, while bluestone accents, wide ash plank floors, and three fireplaces keep it warm and grounded. The Eggersmann kitchen with a butler's pantry is as timeless as it is functional, ready for quiet mornings, long lunches, and the kind of dinners that start at golden hour and somehow become tradition. Outside, the 50-foot pool is set discreetly into the bluff-private, protected, yet open water views. Two additional bedrooms are positioned to work like a separate guest cottage-ideal for extended stays or flexible space for work. A loft, multiple decks, and sun-soaked patios make indoor-outdoor living feel natural-because here, the view is the backdrop to everything. The white-stained cedar exterior blends seamlessly with the landscape. From white Italian marble baths to that last ray of sunset on the patio as the sky turns soft over the Sound, this is a home designed to inspire and never lose power with a full house generator.

4105 Soundview Avenue, Mattituck
$2,100,000
5 Beds ⋅ 5 Baths ⋅ 952621 MLS
Introducing a rare opportunity to build your custom dream home at 2200 Laurel Trail, ideally situated within the private Laurel Links community in the heart of Laurel’s sought after North Fork. This to be built residence offers buyers the ability to personalize finishes, layout details, and design elements while securing brand-new construction in an exceptional golf course setting. Occupying a prime .70 acre golf course lot, perfectly positioned backing directly to the fairway, the property offers sweeping views, exceptional privacy, and a serene backdrop of manicured greens. There is ample room for a pool and outdoor entertaining space, allowing you to create a true resort style backyard. Residents of Laurel Links enjoy exclusive access to community amenities including a clubhouse with recreation facilities, resort style pool, tennis courts, and a premier golf course all within a secure, beautifully maintained enclave. Located just moments from North Fork beaches, renowned vineyards, farm stands, and charming local shops, this offering combines lifestyle, luxury, and location. Enjoy the benefits of new construction and the rare opportunity to customize every detail. Now is the time to design and build a home that truly reflects your vision in one of Laurel’s most desirable communities.

2200 Laurel Trail, Laurel
$999,000
962608 MLS
Nestled along the picturesque shores of Long Island Sound, this exquisite property offers a rare opportunity to indulge in the epitome of waterfront living. Boasting panoramic views of the glistening waters and stunning sunsets, this parcel is raised and setback as to where you have the perfect sanctuary of tranquility and elegance. Beach access, world renowned vineyards, farmers markets, shops etc all a stones throw away. There are three cottages all require extensive renovation. Dock is also permitted and ready to go!! Set your appointment today as this will not last long!

1775 Naugles Drive, Mattituck
$995,000
3 Beds ⋅ 2 Baths ⋅ 961542 MLS
Completely renovated in 2025, this charming ranch offers three bedrooms, two baths, and a full basement with egress windows and walk-out access—perfect for future finishing. The home features a fully updated interior and exterior, plus a brand-new backyard patio with a full outdoor kitchen, ideal for entertaining. There is also room on the property for a pool. Residents enjoy exclusive access to Breakwater Beach. Located on the North Fork, this home provides a lifestyle filled with relaxation and charm, with nearby vineyards, farm stands, beaches, and endless opportunities to unwind and explore.

1150 Ruth Road, Mattituck
$399,000
957255 MLS
Tucked away on a serene cul-de-sac in the heart of Mattituck, this prime, shy wooded acre offers a rare blend of privacy, natural beauty, and opportunity. Gently rolling terrain creates the perfect canvas for your custom retreat, while expansive sunset views over neighboring wetlands provide a breathtaking daily backdrop. With the DEC permit and Southold Town Trustee approvals renewals in progress, and the Board of Health permit in place, the groundwork has already been laid for your vision to come to life. Imagine designing and building your ideal North Fork home in this peaceful, sought-after setting.

955 Blossom Bend, Mattituck
$660,000
3 Beds ⋅ 2 Baths ⋅ 954672 MLS
This colonial-style home features three bedrooms, two full baths, an eat-in kitchen, and driveway parking. The information provided is estimated to the best of our abilities at this time.

24635 Main Road, Cutchogue
$2,499,000
3 Beds ⋅ 3 Baths ⋅ 943316 MLS
Set along one of Mattituck’s most sought-after waterfront enclaves, 2280 Deep Hole Drive offers a rare opportunity to own an exquisite waterfront residence newly built in 2022, encompassing 3,000 square feet of thoughtfully designed living space with exceptional deepwater dockage and direct access to Peconic Bay. Perfectly suited for the boating enthusiast, the property features approximately 130 feet of deepwater frontage on Deep Hole Creek and a substantial dock capable of accommodating two vessels up to 36 feet, complete with electric and water, providing protected, convenient access to the bay and beyond. The home features 9-foot ceilings on the main level, an open-concept layout filled with natural light, expansive water views, and refreshing bay breezes throughout. At the heart of the home is a custom chef’s kitchen appointed with premium, professional-grade appliances, high-end finishes, and a large center island ideal for entertaining and everyday living. The kitchen flows seamlessly into the dining and living areas, where a gas fireplace anchors the space with warmth and ambiance while framing serene water views. Sliding doors from the main living areas open to a waterside deck and balcony, creating an ideal setting for alfresco dining or relaxing in the spa-style hot tub overlooking the water. The first-floor primary suite offers a private retreat with an en-suite bath, and then there are 3+ additional spacious bedrooms, dedicated workstation areas, and 2.5 baths that provide flexibility and comfort. A unique music room offers creative space for the artistically inclined and can easily be converted into 2 bedrooms if desired. The full walk-out daylight basement provides expansive storage and the potential for a gym, workshop, or recreational space. Built with enhanced features for comfort and efficiency, the home includes a Navien tankless hot water system, 1,000-gallon propane tank, thermal windows, updated systems throughout, and a whole-house Generac generator for added peace of mind. Outdoors, there is room for a pool, and the waterfront setting creates an exceptional lifestyle opportunity for boating, fishing, paddleboarding, and entertaining by the water. Ideally located less than one mile from Love Lane and just minutes to local vineyards, farm stands, beaches, parks, and acclaimed North Fork dining, 2280 Deep Hole Drive is more than a home—it is a complete waterfront lifestyle defined by modern design, flexible living spaces, coveted dockage, and the unmistakable charm of Mattituck’s North Fork. Includes an option to purchase furnishings. Nearby Pool Club Membership available at Strong’s Water Club and Marina

2280 Deep Hole Drive, Mattituck
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 932413 MLS
17525 County Rd. 48 (aka Middle Rd). Currently being used as a "tree farm", large farmhouse w/high ceilings, open living/dining area, craft room, den and office space. First floor full bath, full row of storage closets. Second floor offers large primary bedroom with high ceilings & 2 additional bedrooms, full bath. Inground pool, large patio area, huge accessory building with large overhead door, 2.06 acres (150 x 600) with partial irrigation zoned AC Agriculture Conservation (Residential). Endless possibilities with large outbuilding for the hobby enthusiast, country farmer or one looking for a serene lifestyle amongst the beautiful North Fork surroundings.

17525 County Road 48, Cutchogue
$3,500,000
929435 MLS
Waterfront Opportunity on the Long Island Sound! Discover the rare chance to own prime waterfront land on esteemed Oregon Road in Cutchogue, AKA the Sunniest spot in New York. Headlining 2.72 acres and over 183 feet of direct water frontage on the Long Island Sound. This exceptional property offers sweeping, unobstructed water views and the serenity of coastal living. Whether you envision a private estate, vacation retreat, or future development, this parcel provides endless potential. Enjoy breathtaking sunsets, gentle sea breezes, and a front-row seat to one of the most coveted shorelines in the region. A truly remarkable opportunity to build your dream home on the North Fork. Price is for land only.

6121 Oregon Road, Cutchogue
$4,995,000
6 Beds ⋅ 7 Baths ⋅ 894818 MLS
Brand new exquisite waterfront 6 bedroom, 7 bathroom home set on 1.33 acres along coveted Mattituck Inlet in the heart of the North Fork, this exceptional waterfront retreat spans approximately 5,920 square feet of refined living space, blending classic Hamptons-style cedar-shingle architecture with a sophisticated, contemporary interior. Designed for both elegance and everyday comfort, the home features an airy open-concept layout anchored by a dramatic great room with soaring ceilings, expansive Andersen 400 Series double-hung windows, and walls of glass framing panoramic water views. A Heat & Glo 36” propane fireplace with tranquil surround, LED lighting, fan blower, and multi-function remote adds warmth and ambiance. The chef’s kitchen is a true showpiece, appointed with full overlay cabinetry with glass-top cabinets extending to the ceiling, quartz countertops, and a premium appliance suite including a 48” Sub-Zero refrigerator, 48” Wolf gas range, 30” Wolf double wall oven, 24” Wolf microwave, and 24” Miele dishwasher—all stainless steel. The kitchen flows seamlessly into the dining area and outdoor entertaining spaces. The primary suite offers a spa-inspired retreat with radiant electric floor heating in the primary and junior primary baths, private terrace access, and serene water views. Wide-plank 7” plain-sawn white oak flooring runs throughout, enhancing the home’s warm yet modern aesthetic. Additional bedrooms are generously sized and thoughtfully designed for privacy and comfort. Outdoor living is exceptional, featuring a heated 20’ x 40’ gunite saltwater pool with jacuzzi, surrounded by imported Marmiro Stone (Afyon Cloud) patios, a mahogany primary deck, covered porch, and landscaped grounds serviced by a 10-zone Hunter irrigation system. The property includes metal and cedar fencing, a private dock, and direct waterfront access—ideal for boating and waterside living. Additional highlights include state-of-the-art, energy efficient, multi zone HVAC (every bedroom and common area has its own thermostat - the system has multiple fans for dedicated zones), central air, public water, septic system, a two-car garage, cedar shingle roof and siding with white double-dipped finish. Surrounded by vineyards, farm stands, and pristine North Fork beaches, this extraordinary waterfront estate delivers modern luxury, timeless craftsmanship, and the relaxed elegance of Long Island’s wine country—an unparalleled opportunity for refined coastal living.

2590 Cox Neck Road, Mattituck
$3,499,000
4 Beds ⋅ 3 Baths ⋅ 923175 MLS
Welcome to your private sanctuary on Long Island’s North Fork. This striking Mediterranean-inspired residence sits on over 2 acres of lush, water-front property, accessible only by driving through a working farm. Ensuring both exclusivity and a bucolic sense of arrival. As you approach, a winding drive sets the tone, with pastoral vistas and mature landscaping revealing the home gracefully perched near the water’s edge. The exterior features classic stucco and terracotta details that evoke timeless Mediterranean architecture. Step inside to a warm and inviting interior, where abundant natural light pours through expansive windows framing serene waterfront views. The main level offers an open living and dining area, ideal for both entertaining and daily living. One of the home’s standout assets is the finished lower level, perfect as a recreation hub, media room, or flexible living space to suit your lifestyle. Outside, the grounds are spectacular, sweeping lawns and multiple terraces lead you down toward the water’s edge. Whether enjoying morning coffee while listening to gentle lapping waves or hosting al fresco dinners under the stars, this property offers truly magical moments.

3400 Dignans Road, Cutchogue
$2,549,000
4 Beds ⋅ 3 Baths ⋅ 908511 MLS
Experience the ultimate in North Fork waterfront living at this captivating 4-bedroom, 3-bathroom retreat on the Peconic Bay. Featured in The New York Times and Rue Magazine, this home was designed by the renowned firm Hyphen & Co. with the vision of making every day feel like a vacation. Set on prime private bay frontage, the residence was thoughtfully crafted to maximize water views from nearly every room. The open-concept main level is the heart of the home, with a modern chef’s kitchen featuring stainless steel appliances, sleek white cabinetry, light countertops, and a spacious island that doubles as a breakfast bar. The adjoining dining area and sun-filled living room create an effortless flow, with large windows and sliders that frame sweeping vistas across the bay to Robins Island and Southampton. The primary suite is a true sanctuary with its own balcony overlooking the water—perfect for sunrise coffee or sunset cocktails. Three additional bedrooms and two well-appointed baths provide plenty of space for family and guests. Each detail, from the wood-finished floors to the custom fixtures, reflects a balance of elegance and comfort. Step outside to an expansive waterside deck designed for unforgettable entertaining, from al fresco dining to nights by the fire pit. With direct access to the bay, enjoy swimming, kayaking, paddleboarding, boating, and fishing just steps from your door. Located minutes from Love Lane, vineyards, farm stands, and fine dining, this property offers the best of North Fork lifestyle—charm, convenience, and unmatched natural beauty. Furnishings included in the sale. Recent premium updates include New roof(full), New upper and lower decks, New siding and upgraded window surrounds, New driveway, New bulkhead cap, New rugs in primary and guest bedrooms, New electric shades, New outdoor composite lighting. Private association beach, full service marina and pool membership club just around the corner and the ability to moor your boat right out front.

4415 Camp Mineola Road, Mattituck
$5,750,000
5 Beds ⋅ 8 Baths ⋅ 907439 MLS
Welcome to Lion’s Gate on the Sound, a premier waterfront estate set on over 3 private, gated acres along the Long Island Sound in Mattituck. This move-in-ready sanctuary blends timeless architecture with modern luxury, offering unmatched privacy and sweeping coastal views. A newly resurfaced driveway leads through electronic gates to beautifully lit grounds featuring a restored gazebo, lush lawns, and thoughtful landscaping. Inside, the home shines with freshly refinished hardwood floors, custom details, and a reimagined primary suite with spa-like finishes. Smart-home automation, new TVs, and elegant upgrades enhance everyday living. The finished lower level offers a professional gym, billiard room, and custom bar, while the upgraded garage with epoxy floors and smart tech is ideal for car enthusiasts. Outdoors, enjoy a new dining pavilion, full irrigation, and multiple vantage points for stunning sunsets over the Sound. Perfectly located near vineyards, farm stands, and charming village life, Lion’s Gate on the Sound is more than a home, it’s a legacy estate of luxury, seclusion, and natural beauty. Pool permit pending.

3875 Hallock Lane, Mattituck
$705,000
3 Beds ⋅ 2 Baths ⋅ 906405 MLS
Step into this cute and cozy country colonial updated and renovated inside and outside in 2023. Anderson windows on the outside for keeping the house toasty and warm. SS appliances in the country kitchen with hardwood floors on the main floor. Three bedrooms upstairs including a full hall bathroom. There is also a wood burning fireplace in the living room to add to the country flavor. Full unfinished basement with an outside entrance to add to your living space. And the location is close to all including shops with the flavor of a truly historic area.! Country living at its best! .

30170 Main Road, Cutchogue
$4,859,000
6 Beds ⋅ 9 Baths ⋅ 894800 MLS
Luxury New Construction at its finest! Located in coveted Nassau Point and situated on nearly two verdant acres, this stately 8,500+ sq. ft. home features three-levels of meticulously crafted living space. The impressive entry foyer immediately sets the tone for grandeur with front to back living room doors, tasteful herringbone oak floors, 10' ceilings, custom mill work and views beyond of the patio through a wall of glistering glass. The lavish designer kitchen showcases a 9' island, Sub-Zero & Wolf appliances, 2 Bosch dishwashers, 3 wine fridges, and a 7x14 cleverly hidden walk-in pantry. Adjacent to this open floor plan is the dining area and the great room with statement gas burning fireplace and floor to ceiling windows and doors accessing over 1,000 square feet of covered and uncovered stone patios. There are six ensuite bedrooms all with radiant heated bathrooms including 2 Primary suites. One is conveniently located in a separate wing on the first floor and the second is located upstairs - boasting a spa-like bathroom and a private 400 square ft. covered terrace. The sun-drenched lower level offers walk-out access to the rear property including an outdoor shower and 18x36 saltwater pool. There is also ample room for tennis courts. The lower level serves as a cabana area with a recreational room and beverage center, gym area, sauna and bonus rooms providing the ideal space for a home theater and wine cellar. Additional features include a whole house generator, a 30X60 stand up attic plus a 3 car garage. This is more than a home - it is a lifestyle. Enjoy multiple expansive sandy beaches just a stone's throw away and all the North Fork is so well known for - vineyards, world class dining, boating, farms and more.

3360 Wunneweta Road, Cutchogue
$2,075,000
L3530560 MLS
Prime Development Parcel In Center of Mattituck's Burgeoning Business District! Multiple Business, Residential & Mixed Use Possibilities. 5 Buildings Possible As of Right. Commercial Listing MLS# 3530701, Additional information: Minimum Plot Size:10000

385 New Suffolk Avenue, Mattituck
$1,999,000
L3562073 MLS
Cutchogue, North Fork - expired Trustee's permit to construct a single-family waterfront residence on superb soundfront lot with incredible Waterview and convenient location with access to all of the best of the North Fork.... Located north of Oregon Road, among the broad fields and vineyards is the site for the development of your North Fork dream home, with 100 feet on the sound and your own beach. Paved road, association beach access (private stairs permitted), water/electric at street. Sit down with your designer/architect and plan your future now - or acquire as an investment. Ass'n stairs to beach below a few doors away.

895 Glen Court, Cutchogue

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.